We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
All 8 Baileys Harbor B&Bs / inns

Orphan Annie's Schoolhouse Inn

8097 School St., Baileys Harbor, WI
Hotel amenities
  • Overview
  • Reviews (16)
  • Photos (7)
  • Q&A
  • Room tips (1)
  • Location
  • More
Orphan Annie's Schoolhouse Inn
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Baileys Harbor
Check In Check Out
Write a Review

16 people have reviewed this hotel

Traveler rating
See reviews for
Rating summary
  • Sleep Quality
    4.5 of 5 stars
  • Location
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room Tips
Date | Rating
  • English first
  • Any
English first
Halstead, Kansas
Top Contributor
136 reviews 136 reviews
18 hotel reviews
31 helpful votes 31 helpful votes
5 of 5 stars Reviewed August 4, 2013 via mobile

We have stayed here every summer, for about the past 15 years, and wouldn't go anywhere else. The rooms are large, impeccably clean and have nice decks. And, yes, Loren and Annie have rules, but that's one reason we stay there. It's just very nice and quiet, and you won't find nicer rooms and better value.

Was this review helpful? Yes 2
Pewaukee, Wisconsin
Senior Reviewer
8 reviews 8 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 8, 2012

I could not have been more pleased with our stay at this inn! From contacting Loren about the room and details to the incredibly clean rooms and grounds. Loren and his wife were very very nice and happy to help you in any way. A lot of charm to this old school house turned inn. Yes the floors are squeaky,... More

Was this review helpful? Yes
Milwaukee, Wisconsin
Senior Reviewer
6 reviews 6 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 7, 2012

I just arrived home from my first stay here. I was slightly hesitant upon my arrival after reading the reviews. I will say that as a WEEKLY business traveler for 5 years I have never seen a cleaner room! We stayed in the Homestead Suite. It was super quiet at night. Baileys Harbor is on the quieter side of the... More

Was this review helpful? Yes
Mokena, Illinois
12 reviews 12 reviews
5 hotel reviews
4 helpful votes 4 helpful votes
3 of 5 stars Reviewed September 5, 2012

Only complaints were the horribly squeaky floors and the worn out bed. You roll to the middle of the bed. Also the bed is advertised as "Queen size". It is a full size bed, not a queen size. The room (Upper Deck) was nicely decorated and comfortably furnished. We weren't given any "rules" and the owners seemed fine. One telling... More

Was this review helpful? Yes
Milwaukee, Wisconsin
1 review
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed July 21, 2012

We found Orphan Annie's at Bailey's Harbor and wanted to reserve for mid July 2013 for a dance festival in Door County. We talked to the innkeepers on Sunday, July 15, 2012 and reserved a room and wrote a check for 1/2 of the amount. We were given the "rules" of no more that 2 guests for only 1 hour... More

Was this review helpful? Yes 2
Top Contributor
115 reviews 115 reviews
39 hotel reviews
84 helpful votes 84 helpful votes
5 of 5 stars Reviewed July 14, 2012

If you don't need a lake view, this is a lovely place to stay. It's one block out of the center of town, so you can walk to the lake in minutes. The old converted school house is on a park and very quiet. The rooms are large and comforable, each with porches. They don't serve breakfast, but they have... More

Was this review helpful? Yes
Madison, Wisconsin
1 review
4 helpful votes 4 helpful votes
1 of 5 stars Reviewed July 10, 2012

My warning system went on alert immediately as there were notes with rules pasted all over the room, including cleaning the shower stall every day. Some friends of ours live in the area and wanted to see the room. Oh my lord, you think we were having a bachelor party the way Loren reacted. We were lectured and scolded as... More

Was this review helpful? Yes 4
Fairfield Glade, Tennessee
Senior Contributor
43 reviews 43 reviews
13 hotel reviews
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed November 18, 2011

We recently stayed here for the second time, and confirmed that it's indeed a wonderful choice. A very unique place, my wife and I stayed in the Library room (was actually the library when the building was a school) which is more like a suite. It has a small kitchen area, walk-in closet and lots of space. It's decorated with... More

Was this review helpful? Yes
Port Washington, Wisconsin
1 review
5 of 5 stars Reviewed August 26, 2011

This inn is a jewel Door Co. My husband and I were thrilled with the space, the hospitality of our hosts Loren and Annie (refrain from reading the bad reviews, please). This inn is aplace for quiet, for a different vacation experience then ordinary lodging. We found it hard to leave, and will certainly return! The deck with the porch... More

Was this review helpful? Yes
Preston, USA
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 13, 2010

Orphan Annie's Schoolhouse Inn is one of the most unique places we've ever stayed. The rooms, decorated in charming "cottage chic" style, are clean, comfortable and "just like home". The grounds at Orphan Annie's are beautiful with abundant, colorful flowers and places to relax outdoors to enjoy the surroundings and the cool breeze off Lake Michigan. The pictures on the... More

Was this review helpful? Yes 1
Owners: What's your side of the story?
If you own or manage Orphan Annie's Schoolhouse Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.
Manage your listing

Been to Orphan Annie's Schoolhouse Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Orphan Annie's Schoolhouse Inn

Address: 8097 School St., Baileys Harbor, WI
Location: United States > Wisconsin > Door County > Baileys Harbor
Also Known As:
Orphan Annie's Schoolhouse Inn Baileys Harbor, Door County, WI

7 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (4)
Room/suite (1)
Hotel & grounds (2)
Other (1)

Management photos: Courtesy of the property manager

All management photos (4)
Other (4)

Questions & Answers

Enter your question for this accommodation's staff to answer. Other travelers may answer as well.
    Posting guidelines

    See which rooms travelers prefer

    Bookmark for later
    Save Saved
    You added Orphan Annie's Schoolhouse Inn to your Saves list